- Absolute stereochemical determination of 1,2-diols via complexation with dinaphthyl borinic acid
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Rapid derivatization of chiral 1,2-diols with dinaphthyl borinic acid (DBA) leads to a cyclic boronate, enabling the absolute stereochemical prediction via exciton-coupled circular dichroic (ECCD) of the naphthyl groups. Aryl- and alkyl-substituted 1,2-diols derivatized with DBA yield a predictable ECCD, which is also in agreement with theoretical predictions derived from computationally minimized structures.
- Torabi Kohlbouni, Saeedeh,Sarkar, Aritra,Zhang, Jun,Li, Xiaoyong,Borhan, Babak
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p. 817 - 823
(2020/03/26)
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- Nitration-Peroxidation of Alkenes: A Selective Approach to β-Peroxyl Nitroalkanes
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Nitration-peroxidation of alkenes for the synthesis of β-peroxyl nitroalkanes has been developed by using tert-butyl nitrite and tert-butyl hydroperoxide. The method presents a new and selective difunctionalization of alkenes to introduce a nitro group and a peroxyl group across the double bonds of alkenes under mild conditions. A radical reaction pathway is proposed by experimental and theoretical studies.
- Chen, Yuanjin,Ma, Yangyang,Li, Liangkui,Jiang, Hao,Li, Zhiping
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p. 1480 - 1483
(2019/02/26)
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- Direct catalytic synthesis of unprotected 2-amino-1-phenylethanols from alkenes by using iron(II) phthalocyanine
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Aryl-substituted amino alcohols are privileged scaffolds in medicinal chemistry and natural products. Herein, we report that an exceptionally simple and inexpensive FeII complex efficiently catalyzes the direct transformation of simple alkenes into unprotected amino alcohols in good yield and perfect regioselectivity. This new catalytic method was applied in the expedient synthesis of bioactive molecules and could be extended to aminoetherification.
- Legnani, Luca,Morandi, Bill
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supporting information
p. 2248 - 2251
(2016/02/18)
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- Catalyst development for organocatalytic hydrosilylation of aromatic ketones and ketimines
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A new family of Lewis basic 2-pyridyl oxazolines have been developed, which can act as efficient organocatalysts for the enantioselective reduction of prochiral aromatic ketones and ketimines with trichlorosilane, a readily available and inexpensive reagent. 1-Isoquinolyl oxazoline, derived from mandelic acid, was identified as the most efficient catalyst of the series, capable of delivering high enantioselectivities in the reduction of both ketones (up to 94% ee) and ketimines (up to 89% ee).
- Malkov, Andrei V.,Stewart-Liddon, Angus J. P.,McGeoch, Grant D.,Ramirez-Lopez, Pedro,Kocovsky, Pavel
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experimental part
p. 4864 - 4877
(2012/07/28)
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- GSK-3BETA INHIBITOR
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For the purpose of providing a GSK-3β inhibitor containing a 2-aminopyridine compound or a salt thereof or a prodrug thereof useful as an agent for the prophylaxis or treatment of a GSK-3β-related pathology or disease, the present invention provides a GSK-3β inhibitor containing a compound represented by the formula (IA): wherein each symbol is as defined in the specification. or a salt thereof or a prodrug thereof.
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Page/Page column 31
(2011/04/13)
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- Fluorescence-based screening of asymmetric acylation catalysts through parallel enantiomer analysis. Identification of a catalyst for tertiary alcohol resolution
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A technique for high-throughput screening of kinetic resolution catalysts is reported. The method relies on carrying simultaneous kinetic resolutions in a multiwell plate format wherein each well contains a unique catalyst and a small amount of a pH-activated fluorescent sensor (3). By conducting experiments such that each catalyst is evaluated in parallel in the presence of each isolated enantiomer, an indication of catalyst activity is obtained on a per enantiomer basis. Catalysts that are highly active for one enantiomer but modestly active for another are then reevaluated in conventional kinetic resolutions. From these screens, a highly selective krel = 46) pentapeptide (4) was obtained for a model secondary alcohol (1). In addition, peptide 10 was found to afford excellent selectivities (krel > 20) for a number of alcohol substrates (9a-9f) in the traditionally challenging tertiary class.
- Jarvo,Evans,Copeland,Miller
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p. 5522 - 5527
(2007/10/03)
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- Regio- and diastereoselective formation of 1,2-azidohydroperoxides by photooxygenation of alkenes in the presence of azide anions
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1,2-Azidohydroperoxides are accessible from alkenes when irradiated in the presence of azide anions, oxygen and an appropriate sensitizer. The results of substrate/sensitizer variations indicate a reaction initiated by electron transfer to give the sensitizer radical anion and azidyl radicals. The latter efficiently add to alkenes producing carbon radicals which are trapped by molecular oxygen.
- Griesbeck, Axel G.,Hundertmark, Thomas,Steinwascher, Joerg
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p. 8367 - 8370
(2007/10/03)
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- Synthetic Versatility of N(Silylmethyl)imines: Water-Induced Generation of N-Protonated Azomethine Ylides of Nonstabilized Type and Fluoride-Induced Generation of 2-Azallyl Anions
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N-(Silylmethyl)imines generate N-protonated azomethine ylides of nonstabilized type when treated with water in HMPA, which undergo stereospecific and regioselective cycloadditions with electron-poor olefins affording N-unsubstituted pyrrolidines.On the other hand, fluoride-induced desilylation of the imines leads to 2-azallyl anions which are found to be synthetic equivalents of aminomethyl anion in the Michael additions with electron-poor olefins and nucleophilic additions with carbonyl compounds.
- Tsuge, Otohiko,Kanemasa, Shuji,Hatada, Akira,Matsuda, Koyo
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p. 2537 - 2546
(2007/10/02)
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- UTILISATION EN SYNTHESE ORGANIQUE DE MeSi(CN)3 PREPARE IN SITU
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We report the first synthesis of tricyanohydrines by using MeSi(CN)3 prepared "in situ" as reagent, and their potential use as acyl anion or as intermediates in the preparation of β-aminoethyl alcohols.
- Duboudin, F.,Cazeau, P.,Babot, O.,Moulines, F.
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p. 4335 - 4336
(2007/10/02)
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